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Synthesis of 5‐deuteromethyl‐2′‐deoxyuridine (thymidine‐α,α,α‐d 3 ) and related compounds
Author(s) -
Shiue C.Y.,
Wolf A. P.,
Slatkin D. N.
Publication year - 1980
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580170204
Subject(s) - chemistry , thymidine , thymine , deoxyuridine , pyrimidine , iodide , in vivo , kinetics , lithium chloride , chloride , stereochemistry , in vitro , dna , biochemistry , organic chemistry , physics , microbiology and biotechnology , quantum mechanics , biology
Thymine‐α,α,α‐d 3 ( 4 ) was synthesized from perdeuterated methyl iodide and pyrimidine‐lithium. Thymidine‐α,α,α‐d 3 ( 8 ) was then synthesized by coupling compound 4 with 1α‐chloro‐2‐deoxy‐3,5‐bis(p‐toluoyl)‐α‐D‐ribofuranosyl chloride in the presence of Friedal‐Crafts catalyst. Thymidine‐α,α,α‐d 3 ( 8 ), a metabolic precursor of deoxyribonucleic acid, has potential application for study of human tissue growth kinetics in vivo using a sensitive deuterium micromapping technique.